Cameron Diaz Dating History: Complete Timeline of Ex-Boyfriends

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Throughout her career, Cameron Diaz has not only been known for her successful acting, comedic charm, and radiant beauty, but also for her notable relationships with various famous personalities. Here’s a look back at the intriguing dating history of Cameron Diaz:

Carlos de la Torre – Cameron Diaz dated this video producer early in her career before she became a household name.
Matt Dillon – Diaz dated actor Matt Dillon from 1995 to 1998 after meeting him on the set of “There’s Something About Mary.” Dillon was her co-star in the movie.
Jared Leto – The actress and musician Jared Leto had a quiet relationship from 1999 to 2003, during which they were even rumored to be engaged.
Justin Timberlake – The pair became one of the hottest Hollywood couples when they started dating in 2003, working together in “Shrek the Third” before parting ways in 2006.
Alex Rodriguez – Although short-lived, her relationship with the baseball star in 2010 made headlines, intriguing fans and media alike.
Benji Madden – The Good Charlotte band member married Cameron Diaz in 2015 after a relatively private whirlwind romance.

Despite her high-profile relationships, Cameron Diaz has often maintained a sense of privacy. Her eventual marriage to Benji Madden marks a lasting, significant chapter in her personal life, with the couple welcoming a daughter in 2019, and a son in 2024. Diaz remains happily focused on her family, enjoying the joys of parenting and her life away from the Hollywood limelight.

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Cameron Diaz met video producer Carlos De Le Torre for a photoshoot for LA Gear in 1990 and began dating him before landing her big role in The Mask alongside Jim Carrey in 1994. The couple had a long romance that lasted until 1994, when she became well-known in Hollywood.

Cameron Diaz and Matt Dillon were involved in a relationship in the late 1990s. The couple began dating in 1995, and their romance lasted for about three years. Their relationship garnered significant media attention, especially as both were prominent figures in Hollywood at the time. They even worked together professionally during their relationship, most notably co-starring in the hit 1998 comedy “There’s Something About Mary.” Despite their on-screen chemistry and the public’s interest in their relationship, Diaz and Dillon eventually parted ways in 1998.

Cameron Diaz and Jared Leto were romantically linked in the late 1990s and early 2000s, during a period when both actors were rising stars in Hollywood. The pair reportedly began dating in 1999 and were often seen together at various industry events and red carpet appearances, which fueled speculation about the seriousness of their relationship. Despite maintaining a relatively low profile compared to some celebrity couples, they became one of the notable pairs of that era, capturing the attention of fans and media alike. However, by 2003, they had ended their relationship, with both moving on to pursue their burgeoning careers and personal lives separately.

Cameron Diaz and Justin Timberlake were one of Hollywood’s most talked-about couples during their time together in the early 2000s. They began dating in 2003 and were often seen as a glamorous pair, frequently appearing at events and in the media spotlight. The relationship lasted nearly four years, filled with mutual admiration and respect, despite the challenges of being in the public eye. Both Diaz and Timberlake maintained their individual successful careers while supporting each other’s endeavors. In January 2007, they announced their amicable split, emphasizing that they remained friends. Their subsequent interactions, such as working together on the 2011 film “Bad Teacher,” demonstrated their continued professional respect.

Cameron Diaz and Alex Rodriguez were involved in a relationship from 2010 to 2011. The couple, both prominent figures in the entertainment and sports worlds respectively, attracted significant media attention during their time together. They were often seen at various public events, including awards ceremonies and sports games, showcasing a glamorous partnership. Despite the public interest, the relationship was relatively private, and both have since moved on to different partners, with Alex Rodriguez’s subsequent engagement to Jennifer Lopez being among the most notable.

Cameron Diaz and Benji Madden have cultivated a strong and private relationship since they began dating in 2014. The actress and the musician reportedly met through Madden’s sister-in-law, Nicole Richie, and quickly formed a deep connection. They got engaged just a few months later and tied the knot in January 2015 in an intimate ceremony at their Beverly Hills home. Known for valuing their privacy, the couple has maintained a low public profile, often emphasizing the importance of family and personal time away from the spotlight. In December 2019, they welcomed their first child, then in March 2024, they welcomed their second child, son Cardinal.

FAQ

Who was Cameron Diaz's first high-profile relationship?

Cameron Diaz's first widely known high-profile relationship was with Matt Dillon. They dated from 1995 to 1998 after meeting on the set of "There's Something About Mary."

Did Cameron Diaz ever date Justin Timberlake?

Yes, Cameron Diaz and Justin Timberlake dated from 2003 to 2007. They met at the Nickelodeon Kids' Choice Awards and were seen as one of Hollywood's most popular couples during their time together.

Who is Cameron Diaz currently married to?

Cameron Diaz is currently married to Benji Madden, the guitarist of the band Good Charlotte. The couple tied the knot in January 2015, following a whirlwind romance that started in mid-2014.